EP2639216A4 - Halogenated indenones and method for producing optically active indanones or optically active indanols by using same - Google Patents

Halogenated indenones and method for producing optically active indanones or optically active indanols by using same

Info

Publication number
EP2639216A4
EP2639216A4 EP11839101.0A EP11839101A EP2639216A4 EP 2639216 A4 EP2639216 A4 EP 2639216A4 EP 11839101 A EP11839101 A EP 11839101A EP 2639216 A4 EP2639216 A4 EP 2639216A4
Authority
EP
European Patent Office
Prior art keywords
optically active
indenones
indanols
indanones
halogenated
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP11839101.0A
Other languages
German (de)
French (fr)
Other versions
EP2639216B1 (en
EP2639216A1 (en
Inventor
Shohei Yamamoto
Masakatsu Nishihachijo
Rie Tanaka
Shigeru Kawano
Akio Fujii
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kaneka Corp
Original Assignee
Kaneka Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kaneka Corp filed Critical Kaneka Corp
Publication of EP2639216A1 publication Critical patent/EP2639216A1/en
Publication of EP2639216A4 publication Critical patent/EP2639216A4/en
Application granted granted Critical
Publication of EP2639216B1 publication Critical patent/EP2639216B1/en
Not-in-force legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/687Unsaturated compounds containing a keto groups being part of a ring containing halogen
    • C07C49/697Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00Asymmetric syntheses
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/17Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • C07C29/175Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of an oxo group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D241/00Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40Radicals substituted by oxygen atoms
    • C07D307/46Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00Preparation of oxygen-containing organic compounds
    • C12P7/02Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/22Preparation of oxygen-containing organic compounds containing a hydroxy group aromatic
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00Preparation of oxygen-containing organic compounds
    • C12P7/24Preparation of oxygen-containing organic compounds containing a carbonyl group
    • C12P7/26Ketones
    • C12P7/38Cyclopentanone- or cyclopentadione-containing products
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07Optical isomers
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00Systems containing two condensed rings
    • C07C2602/02Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP11839101.0A 2010-11-09 2011-11-08 Halogenated indenones and method for producing optically active indanones or optically active indanols by using same Not-in-force EP2639216B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2010251095 2010-11-09
PCT/JP2011/075767 WO2012063843A1 (en) 2010-11-09 2011-11-08 Halogenated indenones and method for producing optically active indanones or optically active indanols by using same

Publications (3)

Publication Number Publication Date
EP2639216A1 EP2639216A1 (en) 2013-09-18
EP2639216A4 true EP2639216A4 (en) 2014-12-10
EP2639216B1 EP2639216B1 (en) 2018-07-11

Family

ID=46050984

Family Applications (1)

Application Number Title Priority Date Filing Date
EP11839101.0A Not-in-force EP2639216B1 (en) 2010-11-09 2011-11-08 Halogenated indenones and method for producing optically active indanones or optically active indanols by using same

Country Status (5)

Country Link
EP (1) EP2639216B1 (en)
JP (2) JP5941410B2 (en)
CN (2) CN103209949B (en)
DK (1) DK2639216T3 (en)
WO (1) WO2012063843A1 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR094054A1 (en) 2012-12-19 2015-07-08 H Lundbeck As 6-CHLORINE-3- (FENIL-D₅) -INDEN-1-ONA AND USE OF THE SAME
CN106011094B (en) * 2016-07-27 2020-11-03 苏州汉酶生物技术有限公司 Engineered ketoreductase polypeptide and method for preparing (3R,5S) -6-chloro-3, 5-dyhydroxyl hexanoic acid tert-butyl ester by using same
WO2020114853A1 (en) 2018-12-03 2020-06-11 H. Lundbeck A/S Prodrugs of 4-((1r,3s)-6-chloro-3-phenyl-2,3-dihydro-1h-inden-1-yl)-1,2,2-trimethylpiperazine and 4-((1/r,3s)-6-chloro-3-(phenyl-d5)-2,3-dihydro-1h-inden-1-yl)-2,2-dimethy-1-(methyl-d3)piperazine
CN111261786B (en) * 2020-01-19 2023-07-28 浙江大学 Efficient organic solar cell based on asymmetric end-capped electron acceptor

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK55192D0 (en) 1992-04-28 1992-04-28 Lundbeck & Co As H 1-piperazino-1,2-dihydroindene derivatives
KR100266920B1 (en) 1992-08-10 2003-12-31 가네가후치 가가쿠고교 가부시키가이샤 DNA encoding decarbamylase with improved heat resistance and use thereof
JP4753273B2 (en) 1999-07-21 2011-08-24 株式会社カネカ Method for producing optically active pyridine ethanol derivative
CZ20012792A3 (en) 1999-12-03 2002-03-13 Kaneka Corporation Polypeptide, polynucleotide encoding polypeptide, expression vector, transformant and preparation process
SE9904850D0 (en) * 1999-12-30 1999-12-30 Pharmacia & Upjohn Ab Novel process and intermediates
AU2003264502A1 (en) 2002-09-19 2004-04-08 Kaneka Corporation Novel carbonyl reductase, gene thereof and method of using the same
BRPI0413595B8 (en) * 2003-08-18 2021-05-25 H Lundbeck As malonate salt, pharmaceutical composition, use of a malonate salt, and method of manufacturing a compound
ME00154B (en) * 2003-08-18 2010-10-10 H Lundbeck As Succinate and malonate salt of trans-4-(ir,3s)-6-chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine and the use as a medicament
CN1993464B (en) 2004-08-06 2011-12-28 株式会社钟化 Novel carbonyl reductase, gene thereof and method of using the same
WO2006033333A1 (en) 2004-09-24 2006-03-30 Kaneka Corporation Method of producing aldonic acids and aldose dehydrogenase
EP1811021A4 (en) 2004-10-27 2008-05-28 Kaneka Corp Novel carbonyl reductase, gene therefor and use thereof
TWI453198B (en) 2005-02-16 2014-09-21 Lundbeck & Co As H Process for making the trans-1-( (1r , 3s)- 6-chloro - 3 -phenylindan-1- yl ) - 3 , 3 - dimethylpiperazine and salts thereof and for making 4 -((1r , 3s )-6- chloro- 3- phenylindan -1- yl )-1, 2 , 2 -trimethylpiperazine and salts thereof
JP2006262767A (en) 2005-03-24 2006-10-05 Kaneka Corp New glucose dehydrogenase
US20100003732A1 (en) * 2005-05-31 2010-01-07 Kaneka Corporation Process for production of optically active 2-substituted propanal derivative
JP5005672B2 (en) 2006-02-28 2012-08-22 株式会社カネカ Novel carbonyl reductase, gene thereof, and method for producing optically active alcohol using them
WO2007099994A1 (en) 2006-03-02 2007-09-07 Kaneka Corporation Novel carbonyl reductase, gene for the reductase, vector, transformant, and method for production of optically active alcohol utilizing these materials
JP5261172B2 (en) 2006-03-31 2013-08-14 株式会社カネカ Method for producing erythro or threo-2-amino-3-hydroxypropionic ester, novel carbonyl reductase, gene, vector, transformant thereof, and method for producing optically active alcohol using them
JP5308163B2 (en) 2006-11-29 2013-10-09 株式会社カネカ Novel alcohol dehydrogenase, its gene, vector, transformant, and method for producing optically active alcohol using them
US20100292292A1 (en) * 2007-09-13 2010-11-18 Link Medicine Corporation Treatment of Neurodegenerative Diseases Using Indatraline Analogs
EP2202303B1 (en) 2007-09-26 2016-10-26 Kaneka Corporation Novel glucose dehydrogenase
JP2010130912A (en) 2008-12-02 2010-06-17 Kaneka Corp Method for producing optically active 3-quinuclidinol

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
JAMES F. FREEMAN ET AL.: "3-Phenylindones. I. The synthesis of 6-chloro-3-(p-chlorophenyl)-1-indenone and some related compounds", J. AM. CHEM. SOC., vol. 72, 1950, pages 1522 - 1526, XP002721657 *
S.C. PAKRASHI ET AL.: "The Reformatsky reaction on 1-naphthyl-2-bromophenyl ketone", TETRAHEDRON, vol. 18, 1962, pages 1243 - 1249, XP002721656 *
See also references of WO2012063843A1 *

Also Published As

Publication number Publication date
WO2012063843A1 (en) 2012-05-18
CN104496780A (en) 2015-04-08
JPWO2012063843A1 (en) 2014-05-12
JP6093427B2 (en) 2017-03-08
JP5941410B2 (en) 2016-06-29
DK2639216T3 (en) 2018-09-24
EP2639216B1 (en) 2018-07-11
JP2016074712A (en) 2016-05-12
CN103209949B (en) 2016-08-10
EP2639216A1 (en) 2013-09-18
CN103209949A (en) 2013-07-17

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